Multi-step reaction with 6 steps
1: 1.) potassium tert-butoxide / 1.) dioxane, RT, 1.5 h, 2.) dioxane, RT, 22 h
2: p-toluenesulfonic acid monohydrate / dioxane; H2O / 14 h / Heating
3: 1.) n-butyllithium / 1.) hexane, ether, -78 deg C, 20 min, 2.) hexane, ether, from -78 deg C to 0 deg C, 2 h
4: 75 percent / pyridinium chlorochromate, 3-A molecular sieves / CH2Cl2 / 4 h / Ambient temperature
5: 1.) LDA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, from -78 deg C to -20 deg C, 1.5 h
6: 79 percent / triphenyltin hydride, AIBN / benzene / 12 h / Heating
With
n-butyllithium; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; triphenylstannane; potassium tert-butylate; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium diisopropyl amide;
In
1,4-dioxane; dichloromethane; water; benzene;
DOI:10.1021/jo00383a032